α- and β-stannyl trifluoromethylbutenoates: Regioselective preparation and use in copper(I)-catalyzed allylation and propargylation reactions

Advanced Synthesis and Catalysis

Volumn 352, Issue 6, 2010, Pages 949-954

  Carcenac, Yvan ^a   Zine, Khalid ^a   Kizirian, Jean Claude ^a   Thibonnet, Jérôme ^a   Duchêne, Alain ^a   Parrain, Jean Luc ^b   Abarbri, Mohamed ^a  

^a UNIVERSITÉ DE TOURS   (France)

^b CNRS   (France)

Author keywords

Allylation; Copper(I) catalyzed cross coupling; Ethyl trifluorobutynoate; Propargylation; Regioselective hydrostannylation

Indexed keywords

EID: 77951147122     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.200900828     Document Type: Article

References (45)

1. a) R. Filler, Y. Kobayashi, Biomedicinal Aspects of Fluorine Chemistry, Kodansha, Tokyo, 1982;
2. b) M. Hudlicky, Chemistry of Organo Fluorine Compounds, Ellis Horwood, New York, 1976.
3. a) B. E. Smart, Chem. Rev. 1996, 96, 1555-1555;
4. b) G. Resnati, V. A. Soloshonok, Tetrahedron 1996, 52, 1-1;
5. c) Organofluorine Chemistry: Principle and Commercial Applications, (Eds.: R. E. Banks, B. E. Smart, J. C. Tatlow), Plenum Press, New York, 1994.
6. a) M. Prakesh, D. Grée, S. Chandrasekhar, R. Grée, Eur. J. Org. Chem. 2005, 1221-1232;
7. b) K. Mikami, Y. Itoh, M. Yamanaka, Chem. Rev. 2004, 104, 1-16.
8. a) D. J. Burton, Organofluorine chemistry: techniques and synthons, (Ed. : R. D. Chambers), Springer Verlag, Berlin, Heidelberg, 1997;
9. b) J. H. Steenis, A. Gen, J. Chem. Soc. Perkin Trans. 1 2002, 2117-2133;
10. c) G. K. S. Prakash, A. K. Yudin, Chem. Rev. 1997, 97, 757-786;
11. d) I. Ojima, Chem. Rev. 1988, 88, 1011-1030.
12. a) K. Uneyama, C. Noritake, K. Sadamune, J. Org. Chem. 1996, 61, 6055-6057;
13. b) H. Watanabe, F. Yan, T. Sakai, K. Uneyama, J. Org. Chem. 1994, 59, 758-761;
14. c) H. Watanabe, F. Yamashita, K. Uneyama, Tetrahedron Lett. 1993, 34, 1941-1944;
15. d) P. A. Morken, H. Lu, A. Nakamura, D. J. Burton, Tetrahedron Lett. 1991, 52, 4271-4274.
16. T. Kobayashi, T. Nakagawa, H. Amii, K. Uneyama, Org. Lett. 2003, 5, 4297-4300.
17. a) C. R. Davis, D. J. Burton, Organozinc Reagents, (Eds.: P. Knochel, P. Jones), Oxford, 1999, pp 57-76;
18. b) G.-Q. Shi, X.-H. Huang, F. Hong, J. Org. Chem. 1996, 61, 3200-3204;
19. c) P. A. Morken, D. J. Burton, J. Org. Chem. 1993, 58, 1167-1172, and references cited therein.
20. a) R. E. Banks, R. N. Haszeldine, D. R. Taylor, G. Webb, Tetrahedron Lett. 1970, 5215-5218;
21. b) W. Miller, R. H. Snider, R. J. Hummel, J. Am. Chem. Soc. 1969, 91, 6532-6534.
22. a) T. Fuchikami, A. Yamanouchi, I. Ojima, Synthesis 1984, 766-768;
23. b) T. Fuchikami, A. Yamanouchi, Chem. Lett. 1984, 1595-1598.
24. a) Y. Wang, D. J. Burton, Org. Lett. 2006, 8, 1109-1111;
25. b) Y. Wang, L. Lu, D. J. Burton, J. Org. Chem. 2005, 70, 10743-10746;
26. c) J. H. Chae, T. Konno, M. Kanda, T. Ishihara, T. Yamanaka, J. Fluorine Chem. 2003, 120, 185-193.
27. a) M. Abarbri, J. Thibonnet, L. Bérillon, F. Dehmel, M. Rottlander, P. Knochel, J. Org. Chem. 2000, 65, 4618-4634;
28. b) L. Boymond, M. Rottländer, G. Cahiez, P. Knochel, Angew. Chem. 1998, 110, 1801-1803;
29. Angew. Chem. Int. Ed. 1998, 37, 1701-1703.
30. J. Thibonnet, A. Duchêne, J.-L. Parrain, M. Abarbri, J. Org. Chem. 2004, 69, 4262-4264.
31. a) G. Prié, J. Thibonnet, M. Abarbri, A. Duchêne, J.-L. Parrain, Synlett 1998, 839-841;
32. b) B. C. Hamper, Org. Synth. 1991, 70, 246-255.
33. a) K. Tatsuta, T. Yamaguchi, Tetrahedron Lett. 2005, 46, 5017-5020;
34. b) M. Delmas, J. - C. Maire, J. Santamaria, J. Organomet. Chem. 1969, 16, 405-409;
35. c) T. N. Mitchell, A. Amamria, H. Killing, D. Rutschow, J. Organomet. Chem. 1983, 241, C45-C47;
36. d) B. L. Chenard, CM. Van Zyl, J. Org. Chem. 1986, 51, 3561-3566.
37. a) G. Prié, M. Abarbri, J. Thibonnet, J.-L. Parrain, A. Duchêne, New J. Chem. 2003, 27, 432-441;
38. b) F. Camps, R. Canela, J. Coll, A. Messeguer, A. Roca, Tetrahedron 1978, 34, 2179-2182.
39. J. Chen, G.-Q. Lin, Z.-M. Wang, H.-Q. Liu, Synlett 2002, 1265-1268.
40. J. Chen, G.-Q. Lin, Z.-M. Wang, H.-Q. Liu, Synlett 2002, 1265-1268.
41. a) M. Cai, G. Chen, W. Hao, Synthesis 2007, 1197-1203;
42. b) E. Piers, J. G. K. Yee, P. L. Gladstone, Org. Lett. 2000, 2, 481-484;
43. c) E. Piers, E. J. McEachern, P. A. Burns, Tetrahedron 2000, 56, 2753-2765;
44. d) E. Piers, J. G. K. Yee, P. L. Gladstone, E. J. McEachern, Tetrahedron 1998, 54, 10609-10626;
45. e) E. Piers, M. A. Romero, J. Am. Chem. Soc. 1996, 118, 1215-1216, and references cited therein.